3-[(2(S)-Azetidinyl)methoxy]-5-[(1R,2S)-2-(2-methoxyethyl)-cyclopropyl]pyridine

ID: ALA2024095

PubChem CID: 56951497

Max Phase: Preclinical

Molecular Formula: C15H22N2O2

Molecular Weight: 262.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCC[C@@H]1C[C@H]1c1cncc(OC[C@@H]2CCN2)c1

Standard InChI:  InChI=1S/C15H22N2O2/c1-18-5-3-11-7-15(11)12-6-14(9-16-8-12)19-10-13-2-4-17-13/h6,8-9,11,13,15,17H,2-5,7,10H2,1H3/t11-,13+,15-/m1/s1

Standard InChI Key:  NMIIKXFGCKOYRV-OSAQELSMSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
    8.4411   -5.2631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2063   -5.5713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0912   -4.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2985   -5.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2974   -6.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0122   -6.9235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7286   -6.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7258   -5.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0104   -5.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5840   -5.2710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8696   -5.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1550   -5.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9368   -4.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1400   -4.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3537   -5.4821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8676   -5.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5836   -5.6689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2966   -5.2537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2934   -4.4287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  2  0
  4 10  1  0
  1  2  1  0
 10 11  1  0
  5  6  1  0
 12 11  1  1
 12 13  1  0
  2  3  1  0
  6  7  2  0
  1  3  1  0
 13 14  1  0
 14 15  1  0
 15 12  1  0
  1  8  1  6
  7  8  1  0
  2 16  1  1
 16 17  1  0
  8  9  2  0
 17 18  1  0
  9  4  1  0
 18 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2024095

   3-[[(2S)-azetidin-2-yl]methoxy]-5-[(1R,2S)-2-(2-methoxyethyl)cyclopropyl]pyridine

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 262.35

Molecular Weight (Monoisotopic): 262.1681

AlogP: 1.96

#Rotatable Bonds: 7

Polar Surface Area: 43.38

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.79

CX LogP: 0.90

CX LogD: -1.43

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.82

Np Likeness Score: 0.43

References

1. Zhang H, Tückmantel W, Eaton JB, Yuen PW, Yu LF, Bajjuri KM, Fedolak A, Wang D, Ghavami A, Caldarone B, Paterson NE, Lowe DA, Brunner D, Lukas RJ, Kozikowski AP..  (2012)  Chemistry and behavioral studies identify chiral cyclopropanes as selective α4β2-nicotinic acetylcholine receptor partial agonists exhibiting an antidepressant profile.,  55  (2): [PMID:22171543] [10.1021/jm201157c]

Source

Source(1):

• Scientific Literature